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Hawaii Multi-Island Explorer: Waikiki to Kailua-Kona


This is Hawaii for people who refuse to sit still. Enjoy snorkeling, horseback riding, ziplining and more!

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Hawaii: Drink It In

Welcome Aboard the


Stay the night by a private waterfall. Take in the "Road to Hana's" scenic viewpoints. Spend a night on the beach and snorkel the day away. Behold the grandeur of Waimea Canyon. Try on these activities for size: He'eia Bay kayaking, Waikiki sunset sail, Outrigger canoe surfing, 'Akaka Falls and Kulaniapia Falls visit, Volcanoes National Park excursion, snorkeling, horseback riding, ziplining, an optional helicopter ride above the islands, plus free time in Waikiki, Kahului, Hilo and Kona. If you've dreamed of joining a warm group of soon-to-be friends and getting the most out of an active Hawaii adventure, this trip is for you!
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    • Take part in an outrigger canoe surfing adventure. Hop aboard, along with some expert paddlers.
    • Stay in beachfront "tentalows" and snorkel or kayak right from the beach.
    • With basic accommodations, this journey is for those who value sun-drenched activities over comfort.

Travel Curator’s Insights:


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From $7,449 per person
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Jan 14-27, 2024
Feb 4-17, 2024
Feb 18-March 2, 2024
March 3-16, 2024
April 21-May 4, 2024
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Trip Sustainability Awards 



Has launched the Plastics Partnership Project to eliminate the use of single-use plastics



Works closely with The Jane Goodall Institute avoid harming and exploiting wildlife


Local Community

ChildSafe certified and upholds a strict Child Welfare Traveler Code of Conduct


Day 1 - Waikiki

Arrive at any time. Aloha! Welcome to Hawaii. There are no planned activities today, so check into the hotel and spend some time exploring Waikiki. In the evening, join the group for a welcome meeting with your expedition leader.

Your Welcome Moment: Meet Your Expedition Leader and Group

Your opportunity to meet your fellow travelers, and learn more about your tour. Opt to join the group for a local meal afterwards. Don't forget to see the notice in the lobby (or ask reception) for the official time and place to meet up with the group.

Note: This is an example of the hotel we may use in this city. For the actual hotel your specific departure will be using, please check your voucher.

Accommodation: Surfjack Hotel (or similar)

Day 2 - Waikiki

Enjoy a kayaking tour of He'eia Bay. Paddle out to a sand bar and opt to snorkel and spot various fish, turtles and starfish. Return to shore at leisure, then enjoy an included Hawaiian barbecue lunch. Hop back to our hotel to rest and take a dip in the pool, before heading out for a sunset sail and an optional dinner with your expedition leader.

Kane’ohe Bay Kayaking

This morning we head east to Kane’ohe Bay where we will get to kayak the bay and snorkel the hidden sandbars just nearby. Look for turtles and starfish while you snorkel and kayak, or just paddle and enjoy the views of the bay. Afterwards, head back to shore for a traditional Hawaiian Barbecue Lunch.

Waikiki Sunset SailWaikiki

Toast to the setting sun on an evening cruise from Waikiki Beach. Take in the views of Diamond Head and Honolulu, and relax to the sounds of the ocean while slicing through the water. What better way to cap off the day?

Accommodation: Surfjack Hotel (or similar)

Day 3 - Waikiki

Oahu is packed full of things to see and do on this free day. With free time, opt to join the North Shore tour, heading up to Haleiwa town and the north shore food trucks. Or opt to go for a swim at the stunning Hanauma Bay, hike to the top of Diamond Head, take a surf lesson or just hang loose on the beach — Hawaiian-style!

Free Time Waikiki: Hike to the top of Diamond Head for sweeping views of Honolulu, hang ten at a surf lesson, or relax in this seaside paradise – the choice is yours.

Two Optional Activities - Day 3 (Additional cost)

Snorkel Hanauma Bay Waikiki

Head to the crystal waters of Hanauma Bay and rent snorkels to explore the incredible aquatic landscape. This bay is full of a dizzying array of wildlife and can be accessed via public bus.

Diamond Head Hike Waikiki

Hike one of Oahu's most rewarding trails. The top of this volcanic feature offers sweeping 360-degree views as far as the eye can see. This 760-foot summit can be tackled in as little as 40 minutes, making for a great experience with plenty of time for more activities.

Accommodation: Surfjack Hotel (or similar)

Day 4 - Waikiki/Kahului

Fly to the island of Maui. Head over to our campground, where we will be staying in beachfront "tentalows". Spend the rest of the day snorkeling or kayaking right off the beach. Tonight, enjoy a campfire with your fellow travelers.

Private Vehicle Waikiki: Honolulu International Airport

Settle in and scan the scenery from the convenience of a private vehicle.

Plane: Honolulu International Airport – Kahului Airport

Look! Up in the sky! It's a bird! It's a plane! It's... yup, it is a plane, actually.

Private Vehicle: Kahului Airport – Lahaina30m

Settle in and scan the scenery from the convenience of a private vehicle.

Accommodation: Camp Olowalu (or similar campground)

Day 5 - Kahului

Today, take part in an Outrigger Canoe Surfing tour. Learn about the history and cultural significance of these boats, and then hop aboard, along with some expert paddlers, to surf the waves aboard the canoe. Tonight, opt to attend a Luau evening meal and show.

Optional Activity: Luau Lahaina

Music? Check. Traditional Hawaiian feast? Check. Hula? Check! Feel true Hawaiian hookipa (hospitality) at a local luau. This traditional Hawaiian party is world famous and is a must do for any visitor to the islands. Grab a lei and get ready to get down like the locals.

Accommodation: Camp Olowalu (or similar campground)

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Day 6 - Kahului

Travel along the scenic "Road to Hana" towards the east side of Maui. Stop at iconic viewpoints, black volcanic beaches, and every fruit stand along the way! This windy road circumnavigates the island and is the only connection to the small town of Hana on the east side of Maui. Stop by black sand beaches, towering waterfalls, and see how the real islanders live.

Accommodation: Kaanapali Beach Hotel (or similar)

Day 7 - Kahului

Enjoy a full day at leisure. Opt to join the sunrise Haleakala tour, and if you're really feeling up for adventure, take an optional helicopter tour over Molokai Island. Take a full free day to enjoy the best of Maui.

2 Optional Activities - Day 7

Haleakala Sunrise Tour Kahului (Additional Cost)

After an early morning pickup, ascend to the top of Haleakala for a must-see view of the epic Hawaiian sunrise. This tour features a pre-dawn breakfast, a hot brunch buffet and transportation to and from the hotel.

Special Note: Please be aware that if you are interested in participating in the Haleakala Sunrise Tour, we recommend pre-booking this activity well in advance as space can be limited.

Molokai Helicopter Tour Kahului (Additional Cost)

Take to the skies for this 2-island tour of Maui and the nearby island of Molokai, home of the world's largest sea cliffs!

Accommodation: Kaanapali Beach Hotel (or similar)

Day 8 - Kahului/Kapa‘a

Catch a flight to Kauai. After checking into the hotel, get out to start exploring Kauai.

Plane: Kahului Airport – Lihue Airport

Look! Up in the sky! It's a bird! It's a plane! It's... yup, it is a plane, actually.

Optional Welcome Meeting: You may be a seasoned pro at group travel by now, but there will likely be some new travelers joining the group. Sit in on the welcome meeting to meet the newest members of your group and learn about the next leg of your tour.

Accommodation: Kauai Shores Hotel (or similar)

Day 9 - Waimea Canyon

Depart early for a day trip to Waimea Canyon, one of the most iconic areas of Kauai – the rugged valley and colossal cliffs are a sight to behold. On a clear day, look down into Kalalau Valley and the Na Pali Coast to see one of the most remote places on the island. Coined the "Grand Canyon of the Pacific", Waimea Canyon is 10 mi long and 3,600 ft deep. Hike along its winding rim and visit several lookout points to take in the vast beauty of the area.

Waimea Canyon Day Trip - Kapa‘a

Take a day trip to the stunning Waimea Canyon, often called the Grand Canyon of the Pacific. Explore one of the many hiking trails through the canyon as you marvel at the rich colors, lush vegetation and plentiful waterfalls along the canyon walls.

Accommodation: Kauai Shores Hotel (or similar)

Day 10 - Kapa‘a/Hilo

Fly from Kauai to the Big Island. Stop by 'Akaka Falls to stretch your legs, before continuing to our lodge at Kulaniapia Falls. Stop by the Hilo Farmers' Market to stock up on some fresh juice and snacks. Our accommodations are not far from downtown Hilo but will feel miles away. En route to the lodge, stop by 'Akaka Falls. These falls are easy to walk from start to finish and are the perfect introduction to the nature of the Big Island.

Continue to Kulaniapia Falls, our lodge for the next two nights. Built adjacent to a private waterfall, Kulaniapia is a once in a lifetime place. We enjoy our dinner here tonight, overlooking the falls.

Plane: Lihue Airport – Hilo International Airport2h30m

Look! Up in the sky! It's a bird! It's a plane! It's... yup, it is a plane, actually.

Private VehicleHilo International Airport – Hilo: Settle in and scan the scenery from the convenience of a private vehicle.

Visit 'Akaka Falls Visit‘Akaka Falls State Park. ʻAkaka Falls State Park is on Hawaiʻi Island. The park is about 11 miles north from Hilo and it includes ʻAkaka Falls, a 442 feet tall waterfall and loads of fun hiking options.

Accommodation: The Inn Kulaniapia Falls (or similar)

NE Explorer Parked

Day 11 - Hilo

Enjoy a full day at leisure. Sit back and enjoy our private waterfall from the Lanai or choose to rappel down it with a guided tour. Opt to visit a nearby chocolate farm or walk the trails on the property.

Free Time: Hilo - Full Day

Enjoy a full free day to explore the area, or simply relax at the lodge.

Accommodation: The Inn Kulaniapia Falls (or similar)

Day 12 - Hawai‘i Volcanoes National Park 

Depart our waterfall lodge to head to Kona. En route, visit Volcanoes National Park to witness lava flows and Mars-like landscapes. Drive over new lava flows, see newly created black sand beaches, and hike to see cavernous craters. See first-hand how the Hawaiian Islands were formed, and continue to grow! Tonight, opt to swim with Manta Rays in Kona.

Private Vehicle: Hawai‘i Volcanoes National Park – Kailua-Kona Settle in and scan the scenery from the convenience of a private vehicle.

Private Vehicle: Hilo – Hawai‘i Volcanoes National Park Settle in and scan the scenery from the convenience of a private vehicle.

Volcanoes National Park Excursion: Hawai‘i Volcanoes National Park Hawai'i Volcanoes National Park is home to one of the world's most active volcanos, Kilauea. Every day enough lava erupts to cover a 30 km road. Discover the park's lava lakes and tubes and watch as lava flows into the ocean – creating a show of fire and steam!

Optional Activity - Day 12

Manta Ray Evening Snorkel - Kailua-Kona (Additional Cost) One of the most famous snorkeling opportunities in Hawaii, take to the ocean at night and swim with the gentle giant Manta Rays. With potential wingspans of 15 feet and a weight of 1000 pounds, this experience will leave you breathless!

Accommodation: King Kamehameha's Kona Beach Hotel (or similar)

Day 13 - Kailua-Kona

Today is a day at leisure in Kona, and for good reason — Kona is the adventure capital of the Big Island, so there's something to suit everyone here. Opt to go diving, snorkeling, horseback riding, ziplining, or head out to visit a seahorse farm. Tonight, join the group for a final farewell to Hawaii.

If you have always wanted to try Kona coffee and learn a bit more about where it comes from, take a free tour at a nearby farm and buy some beans to take home. Kona is an easy place to stock up on last minute souvenirs, or laze at a cafe and people watch. On the West side of the Big Island, Kona is known for sunsets.

Free Time: Kailua-Kona - Full Day

Enjoy a full free day in the Big Island's adventure capital.

Optional Activity - Day 13

Snorkeling - Slather on the sunscreen and head out into the tantalizing waters. Float effortlessly in the clear warm water and look for schools of fish, coral, sponges and more.

Accommodation: King Kamehameha's Kona Beach Hotel (or similar)

Day 14 - Kailua-Kona

Depart at any time.

Activity Level: Light walking and hiking suitable for most fitness levels. Nothing too challenging. Some optional activities may require higher fitness levels.

Group Size: Small group experience; Max 13, avg 10.

Disclaimer: The information in this trip details document has been compiled with care and is provided in good faith. However, it is subject to change, and does not form part of the contract between the client and the operator. The itinerary featured is correct at time of printing. It may differ slightly to the one in the brochure. Occasionally our itineraries change as we make improvements that stem from past travelers, comments and our own research. Sometimes it can be a small change like adding an extra meal along the itinerary. Sometimes the change may result in us altering the tour for the coming year. Ultimately, our goal is to provide you with the most rewarding experience.

While it is our intention to adhere to the route described above, there is a certain amount of flexibility built into the itinerary and on occasion it may be necessary, or desirable to make alterations. The itinerary is brief, as we never know exactly where our journey will take us. Due to our style of travel and the regions we visit, travel can be unpredictable. The Trip Details document is a general guide to the tour and region and any mention of specific destinations or wildlife is by no means a guarantee that they will be visited or encountered. Additionally, any travel times listed are approximations only and subject to vary due to local circumstances.

Important Air Notes: Please note that on domestic flights within North America, baggage fees are not included in the ticket price and are subject to additional payment at check-in. Should you choose to check a bag on internal flights within Hawaii, the cost is approx. $25 USD (1st checked bag; additional charges if checking more than one bag). Checked bags must be below 50lbs (22.5 kg). We use Hawaii Airlines for our domestic flights on tour. Passengers who enroll in Hawaiian Airlines Rewards Membership program, at least 2 weeks before travel, can reduce the approximate baggage fee from $25USD to $15USD.

Meals Included: 12 breakfasts, 1 lunch, 1 dinner. Other meals will be at your own cost.

Optional Activities & Rates:

- Diamond Head Hike, Waikiki ($7 per person)

- Snorkel Hanauma Bay, Waikiki ($7 per person)

- Luau (No additional cost)

- Haleakala Sunrise Tour, Kahului ($180 per person)

- Molokai Helicopter Tour, Kahului ($309 per person)

- Manta Ray Evening Snorkel, Kailua-Kona ($110 per person)

- Snorkeling (No additional cost)


Life On Board

Deck Plan

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Two people traveling in a room together. Rate is per person. Solos can travel at this rate sharing matched with another traveler.

From in USD:


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Share at the double rate or receive your own single accommodation with the exception of Nights 4 & 5 with this supplement.

From in USD:


This program has a more basic comfort level and multiple activity options. For a certain very independent, active traveler, this will be a fantastic way to experience Hawaii.

Joy Martinello, Founder



What’s Included & Cancellation Policy:

He'eia Bay kayaking tour. Waikiki sunset sail. Outrigger canoe surfing tour. Day trip on the "Road to Hana". Waimea Canyon guided tour. 'Akaka Falls and Kulaniapia Falls visit. Volcanoes National Park excursion. Free time in Waikiki, Kahului, Hilo and Kona. Internal flights. All transportation between destinations and to/from included activities. 12 breakfasts, 1 lunch, 1 dinner. Hotels (11 nts), waterfall lodge (2 nts).

Travel to and from the start and end point of your trip, some beverages, some meals, gratuities, passport and visa fees (if any), optional activities, items of a personal nature (phone calls, laundry and internet, etc.), airline baggage fees, airport and departure taxes (if any), required medical evacuation insurance, optional travel protection insurance.


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